Phosphine, triphenyl-

• Formula: C₁₈H₁₅P
• Molecular weight: 262.2855
• IUPAC Standard InChI: InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Copy

  
• IUPAC Standard InChIKey: RIOQSEWOXXDEQQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 603-35-0
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Triphenylphosphine; Triphenylphosphorus; Trifenylfosfin; Triphenylphosphide; Triphenylphosphane; Phosphorus triphenyl; NSC 10; NSC 215203; PP 360
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Phase change data

Go To: Top, Gas phase ion energetics data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

Go To: Top, Phase change data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Kirklin and Domalski, 1988
Kirklin, D.R.; Domalski, E.S., Enthalpies of combustion of triphenylphosphine and triphenylphosphine oxide, J. Chem. Thermodyn., 1988, 20, 743. [all data]

Forward, Bowden, et al., 1949
Forward, M.V.; Bowden, S.T.; Jones, W.J., Physical Properties of Triphenyl Compounds of Group VB Elements, J. Chem. Soc., 1949, 1949, 121-6. [all data]

Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H., Thermal Energy Studies II. Phenyl Derivatives of Metals, J. Am. Chem. Soc., 1931, 53, 3661-7. [all data]

Kirklin and Domalski, 1988, 2
Kirklin, D.R.; Domalski, E.S., Enthalpies of combustion of triphenylphosphine and triphenylphosphine oxide, J. Chem. Thermodynam., 1988, 20, 743-754. [all data]

Pilcher and Skinner, 1983
Pilcher, G.; Skinner, H.A., Thermochemistry of organometallic compounds, 1983, 43-90, https://doi.org/10.1002/9780470771686.ch2 . [all data]

Bedford and Mortimer, 1960
Bedford, A.F.; Mortimer, C.T., 327. Heats of formation and bond energies. Part II. Triethyl phosphate, triphenylphosphine, and triphenylphosphine oxide, J. Chem. Soc., 1960, 1622, https://doi.org/10.1039/jr9600001622 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Forward, Bowden, et al., 1949, 2
Forward, M.V.; Bowden, S.T.; Jones, W.J., S 26. Physical properties of triphenyl compounds of group V B elements, J. Chem. Soc., 1949, S121, https://doi.org/10.1039/jr949000s121 . [all data]

De Kruif, Herman, et al., 1981
De Kruif, Kees G.; Herman, Johan M.; Van den Berg, Pieter J., Enthalpies of vaporization and vapor pressures of triphenyl-, tri(p-tolyl)- and tris(2-cyanoethyl)phosphines, J. Chem. Eng. Data, 1981, 26, 4, 359-361, https://doi.org/10.1021/je00026a002 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Potapov, Rodionov, et al., 1974
Potapov, V.K.; Rodionov, A.N.; Evlasheva, T.I.; Rogozhin, K.L., Photoionization of triphenyl derivatives of elements in group VB of the periodic table, High Energy Chem., 1974, 8, 486, In original 559. [all data]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. III. Bonding with Group V substituents, Inorg. Chem., 1974, 13, 308. [all data]

Muller and Fenderl, 1969
Muller, J.; Fenderl, K., Massenspektren und Ionisierungspotentiale von C₅H₅Mn(CO)₂PX₃-Komplexen, J. Organometal. Chem., 1969, 19, 123. [all data]

Distefano, Innorta, et al., 1968
Distefano, G.; Innorta, G.; Pignataro, S.; Foffani, A., Correlation between the ionization potentials of transition metal complexes and of the corresponding ligands, J. Organometal. Chem., 1968, 14, 165. [all data]

Vilesov and Zaitsev, 1964
Vilesov, F.I.; Zaitsev, V.M., Photoionization of phenyl derivatives of group 5 elements, Dokl. Akad. Nauk SSSR, 1964, 154, 886, In original 117. [all data]

Ikuta, Kebarle, et al., 1982
Ikuta, S.; Kebarle, P.; Bancroft, G.M.; Chan, T.; Puddephatt, R.J., Basicities of methyl-, methylphenyl-, and phenylphosphines in the gas phase, J. Am. Chem. Soc., 1982, 104, 5899. [all data]

Daamen, Oskam, et al., 1980
Daamen, H.; Oskam, A.; Stufkens, D.J., U.V. photoelectron (He I and He II) studies of M(CO)₅PR₃ (M = Cr, W and R = C₆H₁₁, C₆H₅, O-i-C₃H₇, OC₆H₅) and W(CO)₅As(C₆H₅)₃, Inorg. Chim. Acta, 1980, 38, 71. [all data]

Starzewski and Bock, 1976
Starzewski, K.A.O.; Bock, H., Photoelectron spectra and molecular properties. 58.^1,2 Phosphorus ylides: Gas phase ionization potentials and charge distribution, J. Am. Chem. Soc., 1976, 98, 8486. [all data]

Weiner, Lattman, et al., 1975
Weiner, M.A.; Lattman, M.; Grim, S.O., Ultraviolet photoelectron spectra of some substituted triarylphosphines, J. Org. Chem., 1975, 40, 1292. [all data]

Distefano, Pignataro, et al., 1975
Distefano, G.; Pignataro, S.; Szepes, L.; Borossay, J., Photoelectron spectroscopy study of the triphenyl derivatives of the group V elements, J. Organomet. Chem., 1975, 102, 313. [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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